Compounds and compositions comprising heterocyclic pyrazoline carboxanilides having a &gt;N--N.dbd.C--C(O or S)--N&lt; backbone.
J. Org. Chem., 20, page 1619 (1955) discloses 1,5-diphenyl-2-pyrazoline-3-carboxamide. No utility is presented. Harhash et al., J. Heterocyclic Chem., 21, page 1013 (1984), disclose the preparation of these five pyrazolines for which no utility is presented: ##STR1## where R/Ar are C.sub.6 H.sub.5 /C.sub.6 H.sub.5, CO.sub.2 C.sub.2 H.sub.5 /C.sub.6 H.sub.5, C(O)NHC.sub.6 H.sub.5 /C.sub.6 H.sub.5, CH.dbd.CHC.sub.6 H.sub.5 /C.sub.6 H.sub.5 and CH.sub.3 /4--NO.sub.2 --C.sub.6 H.sub.4.
U.S. Pat. No. 4,070,365 discloses insecticidal compounds of the formula ##STR2## where R.sub.1 is optionally substituted phenyl; R.sub.2 and R.sub.3 are independently optionally substituted pyridyl, thienyl or phenyl groups and X is O or S.
EPA 0153127 discloses insecticidal compounds of the formula ##STR3## wherein A and B are unsubstituted or substituted aryl; U is O, S or NR; Y is alkyl, carbonyl or unsubstituted or substituted aryl, and Z is cycloalkyl or an unsubstituted or substituted aryl group.
PCT International Publication No. WO88/05046 discloses pyrazoline insecticides of the formula ##STR4## wherein: A is H, C.sub.1 to C.sub.6 alkyl, phenyl, phenyl substituted by (R.sub.5).sub.p, CN, CO.sub.2 R.sub.3, C(O)R.sub.3, C(O)NR.sub.3 R.sub.4, C(S)NR.sub.3 R.sub.4, C(S)R.sub.3 or C(S)SR.sub.3 ;
B is H, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 haloalkyl, C.sub.2 to C.sub.6 alkoxyalkyl, C.sub.2 to C.sub.6 cyanoalkyl, C.sub.3 to C.sub.8 alkoxycarbonylalkyl, C.sub.2 to C.sub.6 alkenyl, C.sub.2 to C.sub.6 alkynyl, C.sub.2 to C.sub.6 alkoxycarbonyl, phenyl, phenyl substituted with 1 to 3 substituents independently selected from W, benzyl or benzyl substituted with 1 to 3 substituents independently selected from W. PA0 Y is selected from the group H, C.sub.1 to C.sub.4 alkyl, C.sub.2 to C.sub.4 alkoxyalkyl, C.sub.1 to C.sub.4 alkylthio, C.sub.1 to C.sub.4 haloalkylthio, SX', phenylthio, or phenylthio substituted with 1 to 3 substituents independently selected from W, C.sub.2 to C.sub.4 alkoxycarbonyl, C(O)H, C.sub.2 to C.sub.4 alkylcarbonyl and C.sub.2 to C.sub.4 haloalkylcarbonyl; PA0 A is selected from the group H, C.sub.1 to C.sub.6 alkyl, phenyl, phenyl substituted by (R.sub.5).sub.p, CN, CO.sub.2 R.sub.3, C(O)R.sub.3, C(O)NR.sub.3 R.sub.4, C(S)NR.sub.3 R.sub.4, C(S)R.sub.3, C(S)SR.sub.3 and J; PA0 B is selected from the group H, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 haloalkyl, C.sub.2 to C.sub.6 alkoxyalkyl, C.sub.2 to C.sub.6 cyanoalkyl, C.sub.3 to C.sub.8 alkoxycarbonylalkyl, C.sub.2 to C.sub.6 alkenyl, C.sub.2 to C.sub.6 alkynyl, C.sub.2 to C.sub.6 alkoxycarbonyl, phenyl, phenyl substituted with 1 to 3 substituents independently selected from W, benzyl and benzyl substituted with 1 to 3 substituents independently selected from W; PA0 W is selected from the group halogen, CN, NO.sub.2, C.sub.1 to C.sub.2 alkyl, C.sub.1 to C.sub.2 haloalkyl, C.sub.1 to C.sub.2 alkoxy, C.sub.1 to C.sub.2 haloalkoxy, C.sub.1 to C.sub.2 alkylthio, C.sub.1 to C.sub.2 haloalkylthio, C.sub.1 to C.sub.2 alkylsulfonyl and C.sub.1 to C.sub.2 haloalkylsulfonyl; PA0 R is ##STR6## or K, being K when A is other than J; R.sub.1, R.sub.2 and R.sub.5 are independently selected from the group R.sub.3, halogen, CN, N.sub.3, SCN, NO.sub.2, OR.sub.3, SR.sub.3, S(O)R.sub.3, S(O).sub.2 R.sub.3, OC(O)R.sub.3, OS(O).sub.2 R.sub.3, CO.sub.2 R.sub.3, C(O)R.sub.3, C(O)NR.sub.3 R.sub.4, S(O).sub.2 NR.sub.3 R.sub.4, NR.sub.3 R.sub.4, NR.sub.4 C(O)R.sub.3, OC(O)NHR.sub.3, NR.sub.4 C(O)NHR.sub.3, NR.sub.4 S(O).sub.2 R.sub.3, and when m, n or p is 2, R.sub.1, R.sub.2 or R.sub.5 can be taken together as --OCH.sub.2 O--, --OCF.sub.2 O--, --OCH.sub.2 CH.sub.2 O--, --CH.sub.2 C(CH.sub.3).sub.2 O--, --OCF.sub.2 CF.sub.2 O--, or --CF.sub.2 CF.sub.2 O-- to form a 5- or 6-membered ring; PA0 R.sub.3 is selected from the group H, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 haloalkyl, C.sub.2 to C.sub.4 alkenyl, C.sub.2 to C.sub.4 haloalkenyl, C.sub.2 to C.sub.4 alkynyl, C.sub.2 to C.sub.4 haloalkynyl, C.sub.2 to C.sub.4 alkoxyalkyl, C.sub.2 to C.sub.4 alkylthioalkyl, C.sub.1 to C.sub.4 nitroalkyl, C.sub.1 to C.sub.4 cyanoalkyl, C.sub.3 to C.sub.6 alkoxycarbonylalkyl, C.sub.3 to C.sub.6 cycloalkyl, C.sub.3 to C.sub.6 halocycloalkyl, phenyl, benzyl, or phenyl or benzyl substituted with 1 to 3 substituents independently selected from W; PA0 R.sub.4 is H or C.sub.1 to C.sub.4 alkyl, or when R.sub.3 and R.sub.4 are attached to a single nitrogen atom, they can be taken together as ##STR7## J and K are independently selected from a 5- or 6-membered heteroaromatic rings independently containing 1 or 2 heteroatoms independently selected from 0 to 1 oxygen, 0 to 1 sulfur and 0 to 2 nitrogen atoms, attached via carbon and optionally substituted by one or more substituents independently selected from W; PA0 X' is ##STR8## R.sub.6 and R.sub.10 are independently selected from C.sub.1 to C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.2 to C.sub.6 cyanoalkyl, C.sub.2 to C.sub.6 alkoxyalkyl, C.sub.3 to C.sub.8 alkoxycarbonylalkyl, C.sub.4 to C.sub.8 dialkylaminocarbonylalkyl, phenyl optionally substituted by 1 to 2 substituents selected from W, benzyl optionally substituted by 1 to 2 substituents selected from W, and phenethyl optionally substituted by 1 to 2 substituents selected from W, or R.sub.6 and R.sub.10 can be taken together as (CH.sub.2).sub.4, (CH.sub.2).sub.5 or (CH.sub.2).sub.2 O(CH.sub.2).sub.2, each ring being optionally substituted with 1 to 2 CH.sub.3 ; PA0 R.sub.7 is F, C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.8 dialkylamino, ##STR9## each ring being optionally substituted with 1 to 2 CH.sub.3 ; phenyl optionally substituted by 1 to 2 substituents selected from W, or R.sub.7 is C.sub.1 -C.sub.20 alkoxy, C.sub.1 -C.sub.4 alkoxy substituted by cyano, nitro, C.sub.1 -C.sub.4 alkoxy, C.sub.4 -C.sub.8 alkoxyalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.2 -C.sub.3 alkoxycarbonyl, C.sub.3 -C.sub.5 dialkylaminocarbonyl, phenyl or 1 to 6 halogens, or R.sub.7 is phenoxy optionally substituted by 1 to 2 substituents selected from W, PA0 R.sub.8 and R.sub.9 are independently selected from C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 haloalkyl or phenyl optionally substituted by 1 to 2 substituents selected from W or R.sub.8 and R.sub.9 may be taken together as (CH.sub.2).sub.2, (CH.sub.2).sub.3 or CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 ; PA0 a is 0 to 2; PA0 Y' is O or S; PA0 m is 1 to 3; PA0 n is 0 to 3; and PA0 p is 0 to 3; PA0 R is ##STR10## and A is J. PA0 X is O; PA0 Y is H, CH.sub.3, SCH.sub.3,SSCl.sub.3, SC.sub.6 H.sub.5, 2-(NO.sub.2)C.sub.6 H.sub.4 S, C(O)CH.sub.3, C(O)H, C(O)CF.sub.3, CO.sub.2 CH.sub.3, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5 or SX'; PA0 X' is X.sub.1, X.sub.2, X.sub.3, X.sub.4, X.sub.5 or X.sub.7 ; PA0 R.sub.6 and R.sub.10 are independently selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, phenyl, benzyl or phenethyl each optionally substituted with W or R.sub.6 and R.sub.10 may be taken together as (CH.sub.2).sub.4, (CH.sub.2).sub.5 or (CH.sub.2).sub.2 O(CH.sub.2).sub.2 ; PA0 R.sub.8 and R.sub.9 are independently selected from C.sub.1 -C.sub.3 alkyl and phenyl; PA0 a is 2; PA0 R.sub.3 is C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.2 haloalkyl, C.sub.2 to C.sub.4 alkenyl, C.sub.2 to C.sub.4 haloalkenyl, propargyl, phenyl, benzyl; or phenyl or benzyl substituted with one of F, Cl, Br, CF.sub.3, OCF.sub.2 H, OCF.sub.3 or NO.sub.2 ; PA0 B is H, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 haloalkyl, C.sub.2 to C.sub.6 alkoxyalkyl, C.sub.2 to C.sub.6 cyanoalkyl, C.sub.3 to C.sub.8 alkoxycarbonylalkyl, C.sub.1 to C.sub.6 alkenyl, C.sub.1 to C.sub.6 alkynyl or C.sub.2 to C.sub.6 alkoxycarbonyl; PA0 n is 0 to 2; and PA0 m is 1 to 2. PA0 R.sub.1 is halogen, CN, SCN, NO.sub.2, R.sub.3, OR.sub.3, SR.sub.3, S(O).sub.2 R.sub.3, CO.sub.2 R.sub.3 or C(O)R.sub.3, or when m is 2, R.sub.1 can be taken together as --OCH.sub.2 CH.sub.2 O--, --CH.sub.2 C(CH.sub.3).sub.2 O--, --OCF.sub.2 CF.sub.2 O-- or --CF.sub.2 CF.sub.2 O--; PA0 R.sub.2 is halogen, CN, SCN, NO.sub.2, R.sub.3, OR.sub.3, SR.sub.3, S(O).sub.2 R.sub.3, OC(O)R.sub.3, OS(O).sub.2 R.sub.3, CO.sub.2 R.sub.3, C(O)R.sub.3, C(O)NR.sub.3 R.sub.4, S(O).sub.2 NR.sub.3 R.sub.4 or NR.sub.3 R.sub.4 ; PA0 R.sub.3 is C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.2 haloalkyl, C.sub.2 to C.sub.4 alkenyl, C.sub.2 to C.sub.4 haloalkenyl or propargyl; PA0 R.sub.4 is H or C.sub.1 to C.sub.2 alkyl; PA0 W is halogen, CN, CO.sub.2 CH.sub.3, C(O)NHCH.sub.3, C(O)N(CH.sub.3).sub.2, NO.sub.2, CH.sub.3, CF.sub.3, OCH.sub.3, OCF.sub.2 H, OCF.sub.2 CF.sub.2 H, SCH.sub.3, SCF.sub.2 H, SCF.sub.2 CF.sub.2 H or S(O).sub.2 CH.sub.3 ; PA0 B is H, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 haloalkyl, or C.sub.3 to C.sub.4 alkenyl; PA0 J is ##STR11## optionally substituted by one substituent selected from W; and R.sub.11 is H or C.sub.1 to C.sub.2 alkyl. PA0 Y is H, CH.sub.3, C(O)CH.sub.3, CO.sub.2 CH.sub.3 or SX'; PA0 X' is X.sub.1, X.sub.2, X.sub.3 or X.sub.5 ; PA0 R.sub.6 is C.sub.1 -C.sub.4 alkyl, CF.sub.3, cyclohexyl, phenyl optionally substituted by W, or benzyl optionally substituted by W; PA0 R.sub.7 is F, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.6 haloalkyl, phenyl or phenoxy each optionally substituted by W, C.sub.1 -C.sub.12 alkoxy, dimethylamino or C.sub.1 -C.sub.4 alkoxy substituted with NO.sub.2, C.sub.2 -C.sub.4 alkoxy or 1-6 halogens; PA0 m is 1 or 2 and one substituent is in the 4-position of the phenyl ring; PA0 n is 0, 1 or 2 and one substituent is in the 4-position of the phenyl ring; PA0 R.sub.1 is F, Cl, Br, CF.sub.3, OCF.sub.2 H, OCF.sub.3, CN, or when m is 2, R.sub.1 can be taken together as --CH.sub.2 C(CH.sub.3).sub.2 O-- or --CF.sub.2 CF.sub.2 O--; PA0 R.sub.2 is F, Cl, Br, CN, NO.sub.2, CF.sub.3, CH.sub.3, OCH.sub.3, OCF.sub.2 H, OCF.sub.3, SCH.sub.3, SCF.sub.2 H, S(O).sub.2 CH.sub.3 or N(CH.sub.3).sub.2 ; and PA0 B is H or CH.sub.3. PA0 R is K and PA0 A is C.sub.1 to C.sub.6 alkyl, phenyl, phenyl substituted by (R.sub.5).sub.p, CO.sub.2 R.sub.3, C(O)R.sub.3, C(O)NR.sub.3 R.sub.4, C(S)NR.sub.3 R.sub.4, C(S)R.sub.3 or C(S)SR.sub.3. PA0 X is O; PA0 Y is H, CH.sub.3, SCH.sub.3, SCCl.sub.3, SC.sub.6 H.sub.5, 2-(NO.sub.2)C.sub.6 H.sub.4 S, C(O)CH.sub.3, C(O)H, C(O)CF.sub.3, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5 or SX'; PA0 X' is X.sub.1, X.sub.2, X.sub.3, X.sub.4, X.sub.5 or X.sub.7 ; PA0 R.sub.6 and R.sub.10 are independently selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, phenyl, benzyl or phenethyl each optionally substituted with W or R.sub.6 and R.sub.10 may be taken together as (CH.sub.2).sub.4, (CH.sub.2).sub.5 or (CH.sub.2).sub.2 O(CH.sub.2).sub.2 ; PA0 R.sub.8 and R.sub.9 are independently selected from C.sub.1 -C.sub.3 alkyl and phenyl; PA0 a is 2; PA0 R.sub.3 is C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.2 haloalkyl, C.sub.2 to C.sub.4 alkenyl, C.sub.2 to C.sub.4 haloalkenyl, propargyl, phenyl, benzyl, or phenyl or benzyl each substituted with one of F, Cl, Br, CF.sub.3, OCF.sub.2 H, OCF.sub.3 or NO.sub.2 ; PA0 m is 1 to 2; and PA0 p is 0 to 2. PA0 R.sub.1 is halogen, CN, SCN, NO.sub.2, R.sub.3, OR.sub.3, SR.sub.3, S(O).sub.2 R.sub.3, CO.sub.2 R.sub.3 or C(O)R.sub.3, or when m is 2, R.sub.1 can be taken together as --OCH.sub.2 CH.sub.2 O--, --CH.sub.2 C(CH.sub.3).sub.2 O--, --OCF.sub.2 CF.sub.2 O-- or --CF.sub.2 CF.sub.2 O--; PA0 R.sub.3 is C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.2 haloalkyl, C.sub.2 to C.sub.4 alkenyl, C.sub.2 to C.sub.4 haloalkenyl or propargyl; PA0 R.sub.4 is H or C.sub.1 to C.sub.2 alkyl; PA0 R.sub.5 is halogen, CN, SCN, NO.sub.2, R.sub.3, OR.sub.3, SR.sub.3, S(O).sub.2 R.sub.3, OC(O)R.sub.3, OS(O).sub.2 R.sub.3, CO.sub.2 R.sub.3, C(O)R.sub.3, C(O)NR.sub.3 R.sub.4, S(O).sub.2 NR.sub.3 R.sub.4 or NR.sub.3 R.sub.4 ; PA0 W is halogen, CN, CO.sub.2 CH.sub.3, C(O)NHCH.sub.3, C(O)N(CH.sub.3).sub.2, NO.sub.2, CH.sub.3, CF.sub.3, OCH.sub.3, OCF.sub.2 H, OCF.sub.2 CF.sub.2 H, SCH.sub.3, SCF.sub.2 H, SCF.sub.2 CF.sub.2 H or S(O).sub.2 CH.sub.3 ; PA0 A is C.sub.1 to C.sub.4 alkyl, phenyl, phenyl substituted with (R.sub.5).sub.p, CO.sub.2 R.sub.3, C(O)R.sub.3, C(O)NR.sub.3 R.sub.4 or C(O)N(R.sub.4)phenyl said phenyl optionally substituted with F, Cl, Br, CF.sub.3, OCF.sub.2 H, OCF.sub.3 or NO.sub.2 ; PA0 B is H, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 haloalkyl, or C.sub.3 to C.sub.4 alkenyl; and PA0 K is ##STR12## substituted by at least one substituent selected from W; and R.sub.11 is H or C.sub.1 to C.sub.2 alkyl. PA0 Y is H, CH.sub.3, C(O)CH.sub.3, CO.sub.2 CH.sub.3 or SX'; PA0 X' is X.sub.1, X.sub.2, X.sub.3 or X.sub.5 ; PA0 R.sub.6 is C.sub.1 -C.sub.4 alkyl, CF.sub.3, cyclohexyl, phenyl optionally substituted by W, or benzyl optionally substituted by W; PA0 R.sub.7 is F, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.6 haloalkyl, phenyl or phenoxy optionally substituted by W, C.sub.1 -C.sub.12 alkoxy, dimethylamino or C.sub.1 -C.sub.4 alkoxy substituted with NO.sub.2, C.sub.2 -C.sub.4 alkoxy or 1-6 halogens; PA0 R.sub.1 is F, Cl, Br, CF.sub.3, OCF.sub.2 H, OCF.sub.3, CN, or when m is 2, R.sub.1 can be taken together as --CH.sub.2 C(CH.sub.3).sub.2 O-- or --CF.sub.2 CF.sub.2 O--; PA0 R.sub.5 is F, Cl, Br, CN, NO.sub.2, CF.sub.3, CH.sub.3, OCH.sub.3, OCF.sub.2 H, OCF.sub.3, SCH.sub.3, SCF.sub.2 H, S(O).sub.2 CH.sub.3, S(O).sub.2 CF.sub.2 H, CO.sub.2 CH.sub.3, C(O)NHCH.sub.3, C(O)N(CH.sub.3).sub.2, S(O).sub.2 N(CH.sub.3).sub.2 or N(CH.sub.3).sub.2 ; PA0 A is phenyl or phenyl substituted with (R.sub.5).sub.p ; PA0 B is H or CH.sub.3 ; PA0 m is 1 or 2 and one substituent is in the 4-position of the phenyl ring; and PA0 p is 0, 1 or 2 and one substituent is in the 3 or 4-position of the phenyl ring. PA0 Y is H, CH.sub.3, C(O)CH.sub.3 or CO.sub.2 CH.sub.3 ; PA0 X' is X.sub.1, X.sub.2 or X.sub.5 ; PA0 R.sub.6 is C.sub.1 -C.sub.4 alkyl or phenyl optionally substituted with CH.sub.3 or Cl; PA0 R.sub.7 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.12 alkoxy, dimethylamino or phenyl optionally substituted with CH.sub.3 or Cl; PA0 R.sub.1 is F, Cl, Br, CF.sub.3, OCF.sub.2 H, OCF.sub.3 or CN; PA0 A is CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, C(O)NHCH.sub.3 or C(O)N(CH.sub.3).sub.2 ; PA0 B is CH.sub.3 ; and PA0 m is 1 or 2 and one substituent is in the 4-position of the phenyl ring. PA0 1-(4-chlorophenyl)-5-(2-furanyl)-4,5-dihydro-N-[4-(trifluoromethyl)phenyl]- 1H-pyrazole-3-carboxamide, PA0 1-(5-chloro-2-pyridinyl)-5-(4-fluorophenyl)-4,5-dihydro-N-[4-(trifluorometh yl)phenyl]-1H-pyrazole-3-carboxamide, PA0 1-(5-bromo-2-pyridinyl)-5-(4-fluorophenyl)-4,5-dihydro-N-[4-(trifluoromethy l)phenyl]-1H-pyrazole-3-carboxamide, PA0 1-(4-chlorophenyl)-5-(5-chloro-2-pyridinyl)-4,5-dihydro-5-methyl-N-[4-(trif luoromethyl)phenyl]-1H-pyrazole-3-carboxamide, and PA0 1-(4-chlorophenyl)-5-(5-chloro-2-thienyl)-4,5-dihydro-N-[4-(trifluoromethyl )phenyl]-1H-pyrazole-3-carboxamide.